Highly enantioselective acylation of acyclic meso 1,3-diols through synergistic isothiourea-catalyzed desymmetrization/chiroablative kinetic resolution

Organic Letters

Volumn 17, Issue 9, 2015, Pages 2118-2121

  Merad, Jérémy ^a   Borkar, Prashant ^a   Bouyon Yenda, Tracy ^a   Roux, Christèle ^a   Pons, Jean Marc ^a   Parrain, Jean Luc ^a   Chuzel, Olivier ^a   Bressy, Cyril ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; DIOSPONGIN A; HEPTANE DERIVATIVE; PYRAN DERIVATIVE; THIOUREA;

ACYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

ACYLATION; ALCOHOLS; CATALYSIS; DIARYLHEPTANOIDS; KINETICS; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM; THIOUREA;

EID: 84928891590     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00707     Document Type: Article

References (65)

1. For a complete review, see: Cereghetti, D. M.; Carreira, E. M. Synthesis 2006, 914
2. Patented in 1997, atorvastatin is currently the bestselling drug in the world of all time. Lancet 2011, 378, 1976 (Editorial).
3. For a review, see: Bode, S. E.; Wolberg, M.; Müller, M. Synthesis 2006, 557
4. Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155
5. Confusion between meso compounds and prochiral molecules exists and is persistent in current literature. IUPAC defined in the "Basic Terminology of Stereochemistry" the meso compound as "the achiral member(s) of a set of diastereomers which also includes one or more chiral members": Moss, G. P. Pure Appl. Chem. 1996, 68, 2193
6. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
7. Enriquez-Garcia, A.; Kündig, E. P. Chem. Soc. Rev. 2012, 41, 7803
8. Diaz-de-Villegas, M. D.; Galvez, J. A.; Badorrey, R.; Lopez-Ram-de-Viu, M. P. Chem.-Eur. J. 2012, 18, 13920
9. Arseniyadis, S.; Spivey, A. In Comprehensive Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2013; Chapter 41, Vol. 3, p 1225.
10. Lewis, C. A.; Sculimbrene, B. R.; Xu, Y.; Miller, S. J. Org. Lett. 2005, 7, 3021
11. Yamada, S.; Misono, T.; Iwai, Y.; Masumizu, A.; Akiyama, Y. J. Org. Chem. 2006, 71, 6872
12. Sakakura, A.; Umemura, S.; Ishihara, K. Adv. Synth. Catal. 2011, 353, 1938
13. For a review on acyclic stereocontrol for noncatalyzed reactions, see: O'Brien, A. G. Tetrahedron 2011, 67, 9639
14. For a review, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841
15. For a review, see: Yamada, S.; Fossey, J. S. Org. Biomol. Chem. 2011, 9, 7275
16. For a review, see: Wheeler, S. E. Acc. Chem. Res. 2013, 46, 1029
17. Vedejs, E.; Chen, X. J. J. Am. Chem. Soc. 1996, 118, 1809
18. Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492
19. Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629
20. Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529
21. Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154
22. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226 and refs 16a and 19a
23. Vigneron, J. P.; Dhaenes, M.; Horeau, A. Tetrahedron 1973, 29, 1055
24. Rautenstrauch, V. Bull. Soc. Chim. Fr. 1994, 131, 515
25. Mohr, J. T.; Ebner, D. C.; Stoltz, B. M. Org. Biomol. Chem. 2007, 5, 3571
26. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475
27. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725
28. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351
29. Li, X.; Liu, P.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2008, 130, 13836
30. Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, Y.; Yang, X.; Birman, V. B. J. Org. Chem. 2012, 77, 1722
31. Taylor, J. E.; Bull, S. D.; Williams, J. M. J. Chem. Soc. Rev. 2012, 41, 2109
32. De Rycke, N.; Couty, F.; David, O. R. P. Chem.-Eur. J. 2011, 17, 12852
33. Joannesse, C.; Johnston, C. P.; Concellon, C.; Simal, C.; Philp, D.; Smith, A. D. Angew. Chem., Int. Ed. 2009, 48, 8914
34. West, T. H.; Daniels, D. S. B.; Slawin, A. M. Z.; Smith, A. D. J. Am. Chem. Soc. 2014, 136, 4476 and references therein
35. Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525
36. Birman, V. B.; Jiang, H.; Li, X. Org. Lett. 2007, 9, 3237
37. Armstrong, R. J.; Smith, M. D. Angew. Chem., Int. Ed. 2014, 53, 12822
38. Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2013, 135, 3964
39. Roux, C.; Candy, M.; Pons, J.-M.; Chuzel, O.; Bressy, C. Angew. Chem., Int. Ed. 2014, 53, 766
40. For a review, see: Glueck, D. S. Catal. Sci. Technol. 2011, 1, 1099
41. For a review, see: Lumbroso, A.; Cooke, M. L.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 1890
42. Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63
43. Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861
44. Isolation: Yin, J.; Kouda, K.; Tezuka, Y.; Trans, Q. L.; Miyahara, T.; Chen, Y.; Kadota, S. Planta Med. 2004, 70, 54
45. Chandrasekhar, S.; Shyamsunder, T.; Prakash, J. S.; Prabhakar, A.; Jagadeesh, B. Tetrahedron Lett. 2006, 47, 47
46. Bressy, C.; Allais, F.; Cossy, J. Synlett 2006, 3455
47. Jennings, M. P.; Sawant, K. B. J. Org. Chem. 2006, 71, 7911
48. Yadav, J. S.; Padmavani, B.; Reddy, B. V. S.; Venugopal, C.; Rao, A. B. Synlett 2007, 2045
49. Bates, R. W.; Song, P. Tetrahedron 2007, 63, 4497
50. Kawai, N.; Hande, S. M.; Uenishi, J. Tetrahedron 2007, 63, 9049
51. Wang, H.; Shuhler, B. J.; Xian, M. Synlett 2008, 2651
52. Sabitha, G.; Padmaja, P. Helv. Chim. Acta 2008, 91, 2235
53. Kumaraswamy, G.; Ramakrishna, G.; Naresh, P.; Jagadeesh, B.; Sridhar, B. J. Org. Chem. 2009, 74, 8468
54. Anada, M.; Washio, T.; Watanabe, Y.; Takeda, K.; Hashimoto, S. Eur. J. Org. Chem. 2010, 6850
55. Kumar, R. N.; Meshram, H. M. Tetrahedron Lett. 2011, 52, 1003
56. Stefan, E.; Nalin, A. P.; Taylor, R. E. Tetrahedron 2013, 69, 7706
57. For a review, see: Kuttruff, C. A.; Eastgate, M. D.; Baran, P. S. Nat. Prod. Rep. 2014, 31, 419
58. For a review, see: Giacalone, F.; Gruttadauria, M.; Agrigento, P.; Noto, R. Chem. Soc. Rev. 2012, 41, 2406
59. CCDC 1029496 contains the supplementary crystallographicdata for this paper. These data can be obtained free of charge fromthe Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif.
60. Morandi, B.; Wickens, Z. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2013, 52, 2944
61. Saicic, R. N. Tetrahedron 2014, 70, 8183
62. Young, I. S.; Baran, P. S. Nat. Chem. 2009, 1, 193
63. Candy, M.; Audran, G.; Bienaymé, H.; Bressy, C.; Pons, J.-M. J. Org. Chem. 2010, 75, 1354
64. Candy, M.; Tomas, L.; Parat, S.; Heran, V.; Bienaymé, H.; Pons, J.-M.; Bressy, C. Chem.-Eur. J. 2012, 18, 14267
65. For a review about total syntheses involving an enantioselective organocatalysis, see: Abbasov, M. E.; Romo, D. Nat. Prod. Rep. 2014, 31, 1318